(1α,3β,5Z,7E)-1,3-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-9,10-secochola-5,7,10(19)-triene-24-carboxylic Acid Methyl Ester

Base Information

• Chemical Name: (1α,3β,5Z,7E)-1,3-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-9,10-secochola-5,7,10(19)-triene-24-carboxylic Acid Methyl Ester
• CAS No.: 145372-43-6
• Molecular Formula: C38H68O4Si2
• Molecular Weight: 645.127
• Mol file: 145372-43-6.mol

Synonyms:(1α,3β,5Z,7E)-1,3-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-9,10-secochola-5,7,10(19)-triene-24-carboxylic Acid Methyl Ester;26,27-DidesMethyl-1,3-(tert-butyldiMethylsilyl) (5Z)-Calcitriol 24-Carboxylic Acid Methyl Ester

Chemical Property of (1α,3β,5Z,7E)-1,3-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-9,10-secochola-5,7,10(19)-triene-24-carboxylic Acid Methyl Ester

Chemical Property:

• Boiling Point: 608.3±55.0 °C(Predicted)
• PSA: 44.76000
• Density: 0.97±0.1 g/cm3(Predicted)
• LogP: 11.16580

Purity/Quality:

26,27-Didesmethyl-1,3-(tert-butyldimethylsilyl)(5Z)-Calcitriol24-CarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A novel 1,25-Dihydroxyvitamin D3 analog tested for vitamin D receptor binding affinity.

Technology Process of (1α,3β,5Z,7E)-1,3-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-9,10-secochola-5,7,10(19)-triene-24-carboxylic Acid Methyl Ester

There total 10 articles about (1α,3β,5Z,7E)-1,3-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-9,10-secochola-5,7,10(19)-triene-24-carboxylic Acid Methyl Ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(8E)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene-de-A,B-24(methoxycarbonyl)-cholestane (1219444-01-5) + Trifluoro-methanesulfonic acid (2S,4R)-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-1-methylene-hept-6-ynyl ester (191849-74-8) → 1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether (145372-43-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In tetrahydrofuran; water; at 20 ℃; for 1h;

DOI:10.1002/chem.200902972

Reference yield: 96.0%

1α-<(tert-butyldimethylsilyl)oxy>-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D3 tert-butyldimethylsilyl ether → 1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether (145372-43-6)

Guidance literature:

In 2,2,4-trimethylpentane; for 5h; Heating; in the dark;

DOI:10.1021/jo00053a023

Reference yield: 93.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10(19)-trien-24-oic acid methyl ester (74029-72-4) → 1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether (145372-43-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 2.5h; Ambient temperature;

DOI:10.1016/S0039-128X(97)00040-8

upstream raw materials:

tert-butyldimethylsilyl chloride

(5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-oic acid methyl ester

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol

Downstream raw materials:

calcitriol

(R)-4-Benzenesulfonyl-8-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-nonan-2-ol

Toluene-4-sulfonic acid (R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexyl ester

(1R,3aS,7aR)-1-((R)-5-Benzenesulfonyl-1-methyl-pentyl)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene